Literature DB >> 28337320

Discovery and Assessment of Atropisomers of (±)-Lesinurad.

Jianfei Wang1, Wenqin Zeng1, Shaohua Li1, Liang Shen1, Zhengxian Gu1, Yang Zhang1, Jian Li1, Shuhui Chen1, Xiangbo Jia2.   

Abstract

(+)- and (-)-Lesinurad were isolated as atropisomers from racemic lesinurad for the first time. No interconversion was observed between the two atropisomers under various conditions tested. The two atropisomers showed significant differences in hURAT1 highly expressed HEK293 cell-based inhibition assays, monkey pharmacokinetic studies, and in vitro human recombinant CYP2C9 stability studies. It was speculated that (+)-lesinurad might offer a better hyperuricemia/gout therapy than (-)-lesinurad or the racemate.

Entities:  

Keywords:  Atropisomer; gout; hyperuricemia; lesinurad

Year:  2017        PMID： 28337320      PMCID： PMC5346995          DOI： 10.1021/acsmedchemlett.6b00465

Source DB:  PubMed          Journal:  ACS Med Chem Lett        ISSN： 1948-5875            Impact factor:   4.345


  16 in total

1.  Atroposelective synthesis of axially chiral biaryl compounds.

Authors:  Gerhard Bringmann; Anne J Price Mortimer; Paul A Keller; Mary J Gresser; James Garner; Matthias Breuning
Journal:  Angew Chem Int Ed Engl       Date:  2005-08-26       Impact factor: 15.336

Review 2.  Assessing atropisomer axial chirality in drug discovery and development.

Authors:  Steven R Laplante; Lee D Fader; Keith R Fandrick; Daniel R Fandrick; Oliver Hucke; Ray Kemper; Stephen P F Miller; Paul J Edwards
Journal:  J Med Chem       Date:  2011-09-15       Impact factor: 7.446

3.  Revealing atropisomer axial chirality in drug discovery.

Authors:  Steven R LaPlante; Paul J Edwards; Lee D Fader; Araz Jakalian; Oliver Hucke
Journal:  ChemMedChem       Date:  2011-01-05       Impact factor: 3.466

Review 4.  Investigational drugs for hyperuricemia.

Authors:  Hania Shahid; Jasvinder A Singh
Journal:  Expert Opin Investig Drugs       Date:  2015-06-14       Impact factor: 6.206

Review 5.  EULAR evidence based recommendations for gout. Part I: Diagnosis. Report of a task force of the Standing Committee for International Clinical Studies Including Therapeutics (ESCISIT).

Authors:  W Zhang; M Doherty; E Pascual; T Bardin; V Barskova; P Conaghan; J Gerster; J Jacobs; B Leeb; F Lioté; G McCarthy; P Netter; G Nuki; F Perez-Ruiz; A Pignone; J Pimentão; L Punzi; E Roddy; T Uhlig; I Zimmermann-Gòrska
Journal:  Ann Rheum Dis       Date:  2006-05-17       Impact factor: 19.103

Review 6.  New medications in development for the treatment of hyperuricemia of gout.

Authors:  Cesar Diaz-Torné; Nuria Perez-Herrero; Fernando Perez-Ruiz
Journal:  Curr Opin Rheumatol       Date:  2015-03       Impact factor: 5.006

Review 7.  New therapies for gout.

Authors:  Daria B Crittenden; Michael H Pillinger
Journal:  Annu Rev Med       Date:  2013       Impact factor: 13.739

8.  A retrospective study of the relationship between serum urate level and recurrent attacks of gouty arthritis: evidence for reduction of recurrent gouty arthritis with antihyperuricemic therapy.

Authors:  Akira Shoji; Hisashi Yamanaka; Naoyuki Kamatani
Journal:  Arthritis Rheum       Date:  2004-06-15

9.  The prevalence of hyperuricemia in China: a meta-analysis.

Authors:  Liu B; Wang T; Zhao Hn; Yue Ww; Yu Hp; Liu Cx; Yin J; Jia Ry; Nie Hw
Journal:  BMC Public Health       Date:  2011-10-27       Impact factor: 3.295

10.  ABCG2 dysfunction causes hyperuricemia due to both renal urate underexcretion and renal urate overload.

Authors:  Hirotaka Matsuo; Akiyoshi Nakayama; Masayuki Sakiyama; Toshinori Chiba; Seiko Shimizu; Yusuke Kawamura; Hiroshi Nakashima; Takahiro Nakamura; Yuzo Takada; Yuji Oikawa; Tappei Takada; Hirofumi Nakaoka; Junko Abe; Hiroki Inoue; Kenji Wakai; Sayo Kawai; Yin Guang; Hiroko Nakagawa; Toshimitsu Ito; Kazuki Niwa; Ken Yamamoto; Yutaka Sakurai; Hiroshi Suzuki; Tatsuo Hosoya; Kimiyoshi Ichida; Toru Shimizu; Nariyoshi Shinomiya
Journal:  Sci Rep       Date:  2014-01-20       Impact factor: 4.379
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  8 in total

1.  Leveraging Atropisomerism to Obtain a Selective Inhibitor of RET Kinase with Secondary Activities toward EGFR Mutants.

Authors:  Sean T Toenjes; Valeria Garcia; Sean M Maddox; Gregory A Dawson; Maria A Ortiz; F Javier Piedrafita; Jeffrey L Gustafson
Journal:  ACS Chem Biol       Date:  2019-08-29       Impact factor: 5.100

Review 2.  Atropisomerism in medicinal chemistry: challenges and opportunities.

Authors:  Sean T Toenjes; Jeffrey L Gustafson
Journal:  Future Med Chem       Date:  2018-01-30       Impact factor: 3.808

3.  Enantioselective Synthesis of Pyrrolopyrimidine Scaffolds through Cation-Directed Nucleophilic Aromatic Substitution.

Authors:  Mariel M Cardenas; Sean T Toenjes; Christopher J Nalbandian; Jeffrey L Gustafson
Journal:  Org Lett       Date:  2018-03-21       Impact factor: 6.005

Review 4.  Addressing Atropisomerism in the Development of Sotorasib, a Covalent Inhibitor of KRAS G12C: Structural, Analytical, and Synthetic Considerations.

Authors:  Brian A Lanman; Andrew T Parsons; Stephan G Zech
Journal:  Acc Chem Res       Date:  2022-09-30       Impact factor: 24.466

5.  Atropisomerism in the Pharmaceutically Relevant Realm.

Authors:  Mariami Basilaia; Matthew H Chen; Jim Secka; Jeffrey L Gustafson
Journal:  Acc Chem Res       Date:  2022-09-26       Impact factor: 24.466

6.  Naphthylisoquinoline alkaloids, validated as hit multistage antiplasmodial natural products.

Authors:  Phanankosi Moyo; William Shamburger; Mariëtte E van der Watt; Janette Reader; Ana Carolina C de Sousa; Timothy J Egan; Vinesh J Maharaj; Gerhard Bringmann; Lyn-Marie Birkholtz
Journal:  Int J Parasitol Drugs Drug Resist       Date:  2020-05-24       Impact factor: 4.077

7.  Carbene-catalyzed atroposelective synthesis of axially chiral styrenes.

Authors:  Jia-Lei Yan; Rakesh Maiti; Shi-Chao Ren; Weiyi Tian; Tingting Li; Jun Xu; Bivas Mondal; Zhichao Jin; Yonggui Robin Chi
Journal:  Nat Commun       Date:  2022-01-10       Impact factor: 14.919

Review 8.  Asymmetric Synthesis of Axially Chiral C-N Atropisomers.

Authors:  Patricia Rodríguez-Salamanca; Rosario Fernández; Valentín Hornillos; José M Lassaletta
Journal:  Chemistry       Date:  2022-03-25       Impact factor: 5.020
  8 in total

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